Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates

Mark D. Aparece; Weipeng Hu; James P. Morken

doi:10.1021/acscatal.9b04453

Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates

Mark D. Aparece, Weipeng Hu, James P. Morken^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

Abstract

Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.

Original language	English (US)
Pages (from-to)	11381-11385
Number of pages	5
Journal	ACS Catalysis
Volume	9
Issue number	12
DOIs	https://doi.org/10.1021/acscatal.9b04453
State	Published - Dec 6 2019

Funding

This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands. This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands.

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1021/acscatal.9b04453

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title = "Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates",

abstract = "Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.",

author = "Aparece, {Mark D.} and Weipeng Hu and Morken, {James P.}",

note = "Funding Information: This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands. Funding Information: This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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AU - Aparece, Mark D.

AU - Hu, Weipeng

AU - Morken, James P.

N1 - Funding Information: This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands. Funding Information: This work was supported by the NIH (No. R35-GM1217140). We thank Solvias for a generous donation of MandyPhos ligands. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/12/6

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N2 - Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.

AB - Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.

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Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates

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